1-Formyl-t-3,t-5-dimethyl-r-2,c-6-diphenyl­piperidin-4-one

Ravichandran, K.; Ramesh, P.; Sakthivel, P.; Ponnuswamy, S.; Ponnuswamy, M.N.

doi:10.1107/S1600536810018490

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1505

https://doi.org/10.1107/S1600536810018490

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1-Formyl-t-3,t-5-dimethyl-r-2,c-6-diphenylpiperidin-4-one

K. Ravichandran,^a P. Ramesh,^a P. Sakthivel,^b S. Ponnuswamy ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 23 April 2010; accepted 18 May 2010; online 29 May 2010)

In the title compound, C₂₀H₂₁NO₂, the piperidine ring adopts a distorted boat conformation. The dihedral angle between the two phenyl rings is 61.33 (18)°. In the crystal, intermolecular C—H⋯O interactions link the molecules into zigzag C(5) chains running parallel to [100].

Related literature

For general background to piperidine derivatives, see: Perumal et al. (2001 ); Dimmock et al. (2001 ). For asymmetry parameters, see: Nardelli (1983 ). For puckering parameters, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the synthesis, see: Jeyaraman et al. (1999 ).

Experimental

Crystal data

C₂₀H₂₁NO₂
M_r = 307.38
Orthorhombic, P b c a
a = 7.4303 (4) Å
b = 15.3567 (6) Å
c = 29.6732 (13) Å
V = 3385.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 292 K
0.22 × 0.19 × 0.16 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.983, T_max = 0.988
16882 measured reflections
4198 independent reflections
2097 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.194
S = 1.02
4198 reflections
213 parameters
25 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.98	2.48	3.398 (3)	156
Symmetry code: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810018490/ci5087sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810018490/ci5087Isup2.hkl

checkCIF report

Comment top

Piperidine derivatives are valued heterocyclic compounds in the field of medicinal chemistry. Piperidin-4-ones are reported to possess analgesic, anti-inflammatory, central nervous system (CNS), local anaesthetic, anticancer and antimicrobial activities (Perumal et al., 2001; Dimmock et al., 2001). The crystallographic study of the title compound has been carried out to establish the molecular structure.

In the title molecule (Fig. 1), the piperidine ring adopts a distorted boat conformation; the puckering (Cremer & Pople, 1975) and asymmetry parameters (Nardelli, 1983) are: q₂ = 0.637 (3) Å, q₃ = -0.052 (3) Å, φ₂ = 245.5 (2)° and Δ_s(C2 & C5) = 3.5 (2)°. The C8—C13 and C16—C21 phenyl rings are in axial [C4—C3—C2—C8 = 75.6 (3)°] and equatorial [C4—C5—C6—C16 = -166.8 (2)°] orientations, respectively. The methyl groups attached to atoms C3 and C5 of the piperidine ring are in axial and equatorial orientations [N1—C2—C3—C14 = 69.9 (2)° and N1—C6—C5—C15 = -168.1 (2)°]. The sum of bond angles around atom N1 (359.5°) of the piperidine ring is in accordance with sp² hybridization.

Atom C6 at (x, y, z) acts as a hydrogen-bond donor to atom O2 of the molecule at (x-1/2, y, 1/2-z) forming a zigzag C(5) chain (Bernstein et al., 1995) running along the a axis, as shown in Fig. 2.

Related literature top

For general background to piperidine derivatives, see: Perumal et al. (2001); Dimmock et al. (2001). For asymmetry parameters, see: Nardelli (1983). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the synthesis, see: Jeyaraman et al. (1999).

Experimental top

An ice-cold solution of acetic-formic anhydride prepared from acetic anhydride (10 ml) and 85% formic acid (5 ml) was added slowly to a cold solution of r-2,c-6-diphenyl-t-3,t-5-dimethyl piperidin-4-one (1.395 g, 5 mmol) in benzene (30 ml). The reaction mixture was stirred at room temperature for 5 h. The organic layer was separated, dried over anhydrous Na₂SO₄ and concentrated. The resulting mass was purified and crystallized from benzene- petroleum ether (333-335 K) in the ratio 1:1 (Jeyaraman et al., 1999).

Structure description top

Atom C6 at (x, y, z) acts as a hydrogen-bond donor to atom O2 of the molecule at (x-1/2, y, 1/2-z) forming a zigzag C(5) chain (Bernstein et al., 1995) running along the a axis, as shown in Fig. 2.

For general background to piperidine derivatives, see: Perumal et al. (2001); Dimmock et al. (2001). For asymmetry parameters, see: Nardelli (1983). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the synthesis, see: Jeyaraman et al. (1999).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of the molecules viewed down the b axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

1-Formyl-t-3,t-5-dimethyl-r-2,c-6-diphenylpiperidin-4-one top

Crystal data top

C₂₀H₂₁NO₂	F(000) = 1312
M_r = 307.38	D_x = 1.206 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1246 reflections
a = 7.4303 (4) Å	θ = 1.4–28.4°
b = 15.3567 (6) Å	µ = 0.08 mm⁻¹
c = 29.6732 (13) Å	T = 292 K
V = 3385.9 (3) Å³	Block, colourless
Z = 8	0.22 × 0.19 × 0.16 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	4198 independent reflections
Radiation source: fine-focus sealed tube	2097 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and φ scans	θ_max = 28.4°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→6
T_min = 0.983, T_max = 0.988	k = −20→18
16882 measured reflections	l = −39→38

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.194	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0741P)² + 1.1948P] where P = (F_o² + 2F_c²)/3
4198 reflections	(Δ/σ)_max = 0.001
213 parameters	Δρ_max = 0.37 e Å⁻³
25 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₂₁NO₂	V = 3385.9 (3) Å³
M_r = 307.38	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.4303 (4) Å	µ = 0.08 mm⁻¹
b = 15.3567 (6) Å	T = 292 K
c = 29.6732 (13) Å	0.22 × 0.19 × 0.16 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	4198 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2097 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.988	R_int = 0.030
16882 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	25 restraints
wR(F²) = 0.194	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.37 e Å⁻³
4198 reflections	Δρ_min = −0.23 e Å⁻³
213 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.0192 (4)	0.2060 (2)	0.13459 (14)	0.1697 (16)
O2	0.6395 (3)	0.38855 (13)	0.21978 (6)	0.0841 (6)
N1	0.2046 (3)	0.31856 (13)	0.14813 (8)	0.0690 (6)
C2	0.3721 (3)	0.27494 (15)	0.13546 (9)	0.0645 (7)
H2	0.3426	0.2132	0.1317	0.077*
C3	0.5024 (3)	0.28034 (15)	0.17521 (8)	0.0565 (6)
H3	0.6204	0.2596	0.1651	0.068*
C4	0.5235 (3)	0.37170 (15)	0.19238 (8)	0.0563 (6)
C5	0.3986 (3)	0.44063 (14)	0.17429 (8)	0.0535 (6)
H5	0.4444	0.4570	0.1445	0.064*
C6	0.2059 (3)	0.40703 (16)	0.16730 (8)	0.0586 (6)
H6	0.1498	0.4034	0.1971	0.070*
C7	0.0458 (5)	0.2769 (3)	0.14840 (17)	0.1186 (15)
C8	0.4415 (4)	0.30662 (16)	0.09006 (9)	0.0715 (8)
C9	0.3332 (6)	0.2922 (2)	0.05318 (12)	0.1179 (14)
H9	0.2243	0.2632	0.0569	0.141*
C10	0.3834 (9)	0.3199 (3)	0.01118 (15)	0.1455 (18)
H10	0.3106	0.3078	−0.0135	0.175*
C11	0.5382 (9)	0.3649 (3)	0.00538 (13)	0.1369 (17)
H11	0.5679	0.3869	−0.0229	0.164*
C12	0.6510 (6)	0.3778 (3)	0.04115 (13)	0.1199 (14)
H12	0.7601	0.4065	0.0371	0.144*
C13	0.6019 (5)	0.3479 (2)	0.08344 (10)	0.0854 (9)
H13	0.6794	0.3560	0.1077	0.103*
C14	0.4401 (4)	0.22289 (18)	0.21443 (10)	0.0781 (8)
H14A	0.5236	0.2281	0.2390	0.117*
H14B	0.4348	0.1633	0.2047	0.117*
H14C	0.3229	0.2413	0.2242	0.117*
C15	0.3989 (4)	0.52323 (17)	0.20290 (10)	0.0779 (8)
H15A	0.3343	0.5128	0.2304	0.117*
H15B	0.3418	0.5695	0.1865	0.117*
H15C	0.5207	0.5393	0.2098	0.117*
C16	0.0934 (3)	0.46917 (17)	0.13948 (9)	0.0627 (6)
C17	−0.0611 (4)	0.50498 (19)	0.15754 (11)	0.0781 (8)
H17	−0.0950	0.4895	0.1866	0.094*
C18	−0.1656 (4)	0.5623 (2)	0.13407 (17)	0.1041 (12)
H18	−0.2686	0.5855	0.1472	0.125*
C19	−0.1192 (6)	0.5849 (2)	0.09201 (18)	0.1146 (14)
H19	−0.1902	0.6241	0.0760	0.138*
C20	0.0328 (6)	0.5506 (2)	0.07227 (12)	0.1109 (12)
H20	0.0638	0.5662	0.0430	0.133*
C21	0.1400 (5)	0.4924 (2)	0.09632 (10)	0.0881 (9)
H21	0.2432	0.4694	0.0832	0.106*
H7	−0.076 (5)	0.287 (2)	0.1562 (11)	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.113 (2)	0.099 (2)	0.298 (4)	−0.0455 (18)	−0.089 (2)	0.053 (2)
O2	0.0795 (13)	0.0781 (13)	0.0947 (14)	−0.0123 (10)	−0.0379 (11)	−0.0045 (10)
N1	0.0443 (11)	0.0572 (12)	0.1055 (16)	−0.0146 (10)	−0.0220 (11)	0.0253 (11)
C2	0.0677 (16)	0.0427 (12)	0.0832 (17)	−0.0081 (12)	−0.0297 (13)	0.0010 (12)
C3	0.0484 (12)	0.0515 (13)	0.0695 (14)	−0.0012 (11)	−0.0139 (11)	0.0017 (11)
C4	0.0486 (12)	0.0571 (14)	0.0631 (14)	−0.0099 (11)	−0.0099 (11)	0.0045 (11)
C5	0.0527 (12)	0.0480 (12)	0.0597 (13)	−0.0046 (10)	0.0025 (10)	0.0044 (10)
C6	0.0474 (12)	0.0678 (15)	0.0606 (13)	0.0004 (11)	0.0032 (10)	0.0163 (12)
C7	0.085 (2)	0.078 (2)	0.193 (4)	−0.038 (2)	−0.057 (3)	0.057 (2)
C8	0.096 (2)	0.0484 (13)	0.0705 (17)	0.0024 (14)	−0.0257 (15)	−0.0083 (12)
C9	0.172 (4)	0.095 (2)	0.087 (2)	−0.018 (2)	−0.062 (2)	0.0030 (19)
C10	0.222 (5)	0.127 (4)	0.087 (3)	−0.001 (4)	−0.060 (3)	−0.003 (2)
C11	0.222 (5)	0.120 (3)	0.069 (2)	0.018 (3)	0.006 (3)	−0.008 (2)
C12	0.153 (4)	0.123 (3)	0.083 (2)	−0.004 (3)	0.030 (3)	−0.015 (2)
C13	0.101 (2)	0.089 (2)	0.0661 (17)	−0.0029 (19)	0.0057 (16)	−0.0164 (15)
C14	0.0777 (18)	0.0679 (17)	0.0887 (19)	−0.0093 (14)	−0.0188 (15)	0.0189 (14)
C15	0.094 (2)	0.0595 (16)	0.0801 (18)	0.0007 (15)	0.0063 (16)	−0.0074 (14)
C16	0.0525 (13)	0.0661 (15)	0.0696 (15)	0.0061 (12)	−0.0013 (11)	0.0106 (12)
C17	0.0534 (15)	0.0730 (18)	0.108 (2)	0.0041 (14)	0.0022 (15)	0.0017 (16)
C18	0.0604 (18)	0.070 (2)	0.182 (4)	0.0121 (16)	−0.019 (2)	0.005 (2)
C19	0.095 (3)	0.075 (2)	0.174 (4)	0.011 (2)	−0.054 (3)	0.029 (3)
C20	0.137 (3)	0.098 (3)	0.097 (2)	0.008 (3)	−0.023 (2)	0.037 (2)
C21	0.097 (2)	0.089 (2)	0.0784 (18)	0.0259 (17)	0.0042 (16)	0.0265 (16)

Geometric parameters (Å, º) top

O1—C7	1.180 (5)	C10—H10	0.93
O2—C4	1.213 (3)	C11—C12	1.367 (6)
N1—C7	1.342 (4)	C11—H11	0.93
N1—C2	1.462 (3)	C12—C13	1.385 (4)
N1—C6	1.473 (3)	C12—H12	0.93
C2—C8	1.522 (4)	C13—H13	0.93
C2—C3	1.528 (3)	C14—H14A	0.96
C2—H2	0.98	C14—H14B	0.96
C3—C4	1.501 (3)	C14—H14C	0.96
C3—C14	1.532 (3)	C15—H15A	0.96
C3—H3	0.98	C15—H15B	0.96
C4—C5	1.507 (3)	C15—H15C	0.96
C5—C15	1.526 (3)	C16—C21	1.374 (4)
C5—C6	1.536 (3)	C16—C17	1.381 (4)
C5—H5	0.98	C17—C18	1.365 (4)
C6—C16	1.513 (3)	C17—H17	0.93
C6—H6	0.98	C18—C19	1.341 (5)
C7—H7	0.95 (4)	C18—H18	0.93
C8—C13	1.363 (4)	C19—C20	1.378 (5)
C8—C9	1.376 (4)	C19—H19	0.93
C9—C10	1.369 (6)	C20—C21	1.393 (4)
C9—H9	0.93	C20—H20	0.93
C10—C11	1.353 (7)	C21—H21	0.93

C7—N1—C2	122.1 (3)	C9—C10—H10	119.8
C7—N1—C6	116.3 (3)	C10—C11—C12	119.8 (4)
C2—N1—C6	121.11 (17)	C10—C11—H11	120.1
N1—C2—C8	111.7 (2)	C12—C11—H11	120.1
N1—C2—C3	108.4 (2)	C11—C12—C13	119.6 (4)
C8—C2—C3	116.8 (2)	C11—C12—H12	120.2
N1—C2—H2	106.4	C13—C12—H12	120.2
C8—C2—H2	106.4	C8—C13—C12	121.0 (3)
C3—C2—H2	106.4	C8—C13—H13	119.5
C4—C3—C2	112.28 (19)	C12—C13—H13	119.5
C4—C3—C14	108.2 (2)	C3—C14—H14A	109.5
C2—C3—C14	111.3 (2)	C3—C14—H14B	109.5
C4—C3—H3	108.3	H14A—C14—H14B	109.5
C2—C3—H3	108.3	C3—C14—H14C	109.5
C14—C3—H3	108.3	H14A—C14—H14C	109.5
O2—C4—C3	120.1 (2)	H14B—C14—H14C	109.5
O2—C4—C5	121.8 (2)	C5—C15—H15A	109.5
C3—C4—C5	118.12 (19)	C5—C15—H15B	109.5
C4—C5—C15	112.6 (2)	H15A—C15—H15B	109.5
C4—C5—C6	112.73 (18)	C5—C15—H15C	109.5
C15—C5—C6	110.8 (2)	H15A—C15—H15C	109.5
C4—C5—H5	106.7	H15B—C15—H15C	109.5
C15—C5—H5	106.7	C21—C16—C17	117.9 (3)
C6—C5—H5	106.7	C21—C16—C6	122.2 (2)
N1—C6—C16	111.6 (2)	C17—C16—C6	119.9 (2)
N1—C6—C5	111.58 (19)	C18—C17—C16	122.1 (3)
C16—C6—C5	112.11 (19)	C18—C17—H17	118.9
N1—C6—H6	107.1	C16—C17—H17	118.9
C16—C6—H6	107.1	C19—C18—C17	119.7 (3)
C5—C6—H6	107.1	C19—C18—H18	120.1
O1—C7—N1	125.8 (5)	C17—C18—H18	120.1
O1—C7—H7	94 (2)	C18—C19—C20	120.5 (3)
N1—C7—H7	140 (2)	C18—C19—H19	119.8
C13—C8—C9	118.1 (3)	C20—C19—H19	119.8
C13—C8—C2	124.9 (2)	C19—C20—C21	119.8 (3)
C9—C8—C2	117.0 (3)	C19—C20—H20	120.1
C10—C9—C8	121.0 (4)	C21—C20—H20	120.1
C10—C9—H9	119.5	C16—C21—C20	120.0 (3)
C8—C9—H9	119.5	C16—C21—H21	120.0
C11—C10—C9	120.4 (4)	C20—C21—H21	120.0
C11—C10—H10	119.8

C7—N1—C2—C8	109.2 (3)	C6—N1—C7—O1	−179.9 (4)
C6—N1—C2—C8	−79.4 (3)	N1—C2—C8—C13	117.9 (3)
C7—N1—C2—C3	−120.7 (3)	C3—C2—C8—C13	−7.7 (4)
C6—N1—C2—C3	50.6 (3)	N1—C2—C8—C9	−62.1 (3)
N1—C2—C3—C4	−51.5 (3)	C3—C2—C8—C9	172.3 (3)
C8—C2—C3—C4	75.6 (3)	C13—C8—C9—C10	−1.2 (5)
N1—C2—C3—C14	69.9 (2)	C2—C8—C9—C10	178.8 (4)
C8—C2—C3—C14	−162.9 (2)	C8—C9—C10—C11	−2.3 (7)
C2—C3—C4—O2	−170.3 (2)	C9—C10—C11—C12	4.3 (8)
C14—C3—C4—O2	66.4 (3)	C10—C11—C12—C13	−2.7 (7)
C2—C3—C4—C5	9.2 (3)	C9—C8—C13—C12	2.7 (5)
C14—C3—C4—C5	−114.1 (2)	C2—C8—C13—C12	−177.3 (3)
O2—C4—C5—C15	−16.0 (3)	C11—C12—C13—C8	−0.8 (6)
C3—C4—C5—C15	164.5 (2)	N1—C6—C16—C21	−66.4 (3)
O2—C4—C5—C6	−142.4 (2)	C5—C6—C16—C21	59.5 (3)
C3—C4—C5—C6	38.2 (3)	N1—C6—C16—C17	114.1 (3)
C7—N1—C6—C16	−65.6 (3)	C5—C6—C16—C17	−120.0 (3)
C2—N1—C6—C16	122.6 (2)	C21—C16—C17—C18	−0.5 (4)
C7—N1—C6—C5	168.1 (3)	C6—C16—C17—C18	179.0 (3)
C2—N1—C6—C5	−3.7 (3)	C16—C17—C18—C19	0.3 (5)
C4—C5—C6—N1	−40.9 (3)	C17—C18—C19—C20	0.2 (6)
C15—C5—C6—N1	−168.1 (2)	C18—C19—C20—C21	−0.5 (6)
C4—C5—C6—C16	−166.8 (2)	C17—C16—C21—C20	0.1 (5)
C15—C5—C6—C16	65.9 (3)	C6—C16—C21—C20	−179.4 (3)
C2—N1—C7—O1	−8.2 (6)	C19—C20—C21—C16	0.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.98	2.48	3.398 (3)	156

Symmetry code: (i) x−1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁NO₂
M_r	307.38
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	292
a, b, c (Å)	7.4303 (4), 15.3567 (6), 29.6732 (13)
V (Å³)	3385.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.22 × 0.19 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.983, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	16882, 4198, 2097
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.194, 1.02
No. of reflections	4198
No. of parameters	213
No. of restraints	25
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.23

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.98	2.48	3.398 (3)	156

Symmetry code: (i) x−1/2, y, −z+1/2.

Acknowledgements

KR thanks the TBI Consultancy, University of Madras, India, for the data collection and the management of Kandaswami Kandar's College, Velur, Namakkal, Tamilnadu, India, for the encouragement to pursue the programme.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Dimmock, J. R., Padmanilayam, M. P., Puthucode, R. N., Nazarali, A. J., Motaganahalli, N. L., Zello, G. A., Quail, J. W., Oloo, E. O., Kraatz, H. B., Prisciak, J. S., Allen, T. M., Santhos, C. L., Balsarini, J., Clercq, E. D. & Manavathu, E. K. (2001). J. Med. Chem. 44, 586–593. Web of Science CSD CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Jeyaraman, R., Thenmozhiyal, J. C., Murugadoss, R. & Venkatraj, M. (1999). Indian J. Chem. 38B, 325–336. CAS Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Perumal, R. V., Adiraj, M. & Shanmugapandiyan, P. (2001). Indian Drugs, 38, 156–159. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar